Photocatalytic C–F bond activation in small molecules and polyfluoroalkyl substances

Xin Liu, Arindam Sau, Alexander R. Green, Mihai V. Popescu, Nicholas F. Pompetti, Yingzi Li, Yucheng Zhao, Robert S. Paton (), Niels H. Damrauer () and Garret M. Miyake ()
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Xin Liu: Department of Chemistry, Colorado State University
Arindam Sau: Department of Chemistry, University of Colorado Boulder
Alexander R. Green: Department of Chemistry, Colorado State University
Mihai V. Popescu: Department of Chemistry, Colorado State University
Nicholas F. Pompetti: Department of Chemistry, University of Colorado Boulder
Yingzi Li: Department of Chemistry, Colorado State University
Yucheng Zhao: Department of Chemistry, Colorado State University
Robert S. Paton: Department of Chemistry, Colorado State University
Niels H. Damrauer: Department of Chemistry, University of Colorado Boulder
Garret M. Miyake: Department of Chemistry, Colorado State University

Nature, 2025, vol. 637, issue 8046, 601-607

Abstract: Abstract Organic halides are highly useful compounds in chemical synthesis, in which the halide serves as a versatile functional group for elimination, substitution and cross-coupling reactions with transition metals or photocatalysis1–3. However, the activation of carbon–fluorine (C–F) bonds—the most commercially abundant organohalide and found in polyfluoroalkyl substances (PFAS), or ‘forever chemicals’—is much rarer. Current approaches based on photoredox chemistry for the activation of small-molecule C–F bonds are limited by the substrates and transition metal catalysts needed4. A general method for the direct activation of organofluorines would have considerable value in organic and environmental chemistry. Here we report an organic photoredox catalyst system that can efficiently reduce C–F bonds to generate carbon-centred radicals, which can then be intercepted for hydrodefluorination (swapping F for H) and cross-coupling reactions. This system enables the general use of organofluorines as synthons under mild reaction conditions. We extend this method to the defluorination of PFAS and fluorinated polymers, a critical challenge in the breakdown of persistent and environmentally damaging forever chemicals.

Date: 2025
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DOI: 10.1038/s41586-024-08327-7

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